The do's and don'ts of dating after 50

Dating after 50 comes with a unique set of challenges, says Ronni Berke.

Story highlights

After two marriages Ronni Berke found herself back in the dating arena post-50

Berke encountered challenges as an older online dater, such as outdated photos

She offers some tips for speed dating too: Come prepared, presentable and personable

Berke is undaunted after her foray into the new world of dating and plans to stay "out there"

I never thought I'd be here, but here I am. And let me tell you -- dating at midlife just ain't what it's cracked up to be.

What's that, you say? Internet dating is all the rage! There's no stigma anymore. It makes perfect sense. With our hypercharged careers, family responsibilities, keeping up with the news and working out -- who has the time to meet people anymore? Forget singles bars. What woman in her 50s really enjoys meeting strange men at bars? Oh, wait. Most Internet "first dates" begin at bars. With strange men. Still, the draw is strong. Everybody seems to know somebody who's met her significant other online.

"Marie met the love of her life," said a friend. "She was smart enough to increase her radius of possibilities to 150 miles. And then she found Ben -- only three hours away." Only three hours? What nobody really seems to tell you is that for every online dating success story, there are hundreds of failures: misleading (or outright fraudulent) profiles, years-old photos (at 50, that makes a real difference), awkward conversations, sexual miscues, and clearly incompatible goals.

My situation is fairly typical. After juggling two children and a demanding job, my first marriage ended in divorce. I had given it some hard thinking, but my relationship with my husband, which began when we were both in college, really couldn't make it for the long haul. So I opted out. About a year later, I encountered a friendly, good-looking neighbor, who had just recently become single. Howard became my second husband and the love of my life. That made it all the more crushing when he died of a brain tumor two years into our marriage. Thus began a long period of mourning, in which I helped usher my two daughters into adulthood, and devoted more attention to my career. But I was awfully lonely. It didn't help that I went straight home from work every night and stayed in on weekends.

Ronni Berke

My friends would gently nudge me: "Why don't you just go out more, even with friends?" "Have you checked out JDate?" And the always dependable: "Take a class. You'll meet people." But I was stubborn. Oddly, I'm a very social person. Why was I cutting myself off from the world? My reasoning was this: If I don't do anything, don't "get out there," nothing bad will happen. As in no disappointment, no heartbreak. There's one problem with this line of thinking. Yes, if you don't do anything, nothing bad happens. However, nothing good happens, either. Nothing happens.

So, seven years after my husband's death, I took the plunge. I signed up for online dating and even went to a speed dating session at a local bar.

I approached online dating very seriously, enlisting help from close friends for my profile. It needed a dash of wit, a sprinkling of sass and an attractive photo. But not too much wit, and not too much sass. As for the photo: There's no such thing as too attractive. After everything posted, I got a flood of responses from men. Not because I'm an exceptional catch, but because those who've been on the sites for a while tend to pounce on a new candidate. There were men who lived in other states and countries. (I can't afford to see you. And Skype relationships are pretty two-dimensional.) Men who mentioned sexual details in their profiles. (Yes, we get that sex is important, even in middle age. But this is just too much information!) Men who were grammatically challenged. (Either I'm not worth a coherent sentence or you are unable to compose one.)

My first online date was at a nearby bar. I rushed home from work, put on a new outfit, makeup and perfume, and left the house looking and feeling like a million bucks. I walked into the bar where my date was sitting. Instantly, I could tell he wasn't interested. (Not that I was, either. But since then, I always arrive earlier than the man on a first date to check out, rather than be checked out.) The whole thing went downhill from there. My date spent an hour talking about what a long day he'd had, his allergies, and even checking out attractive women who walked by. Next!

The following night, I met a divorce lawyer for a drink. That job description should have been a red flag, but remember, I was trying to put myself "out there." He walked in and said: "You're a babe!" The last time someone called me a babe was, well, never. Yet, I tried to make the best of it, until he made a pass at me in the elevator. Want to seduce a woman? Trap her in a box and lunge at her. Works every time. Thankfully, I escaped unscathed.

After a few more encounters in which men talked nervously and endlessly about themselves, I met a man who seemed intelligent, attractive and interested in me. We dated for a couple of months. It was good for the ego at first, but turned out not to be a lasting relationship. Note to self: Just because a man doesn't talk about himself all the time doesn't mean he's right for you.

In addition to online dating, I've tried the novel approach of meeting men in person -- at a speed dating event. But it's just different for the boomer set. We're not kids anymore. We don't really do the "hang out, hook up" thing very well. Having a five-minute conversation isn't much of a barometer for a relationship.

Here are my "Speed Dating Dos and Don'ts, For Men of a Certain Age"

-- DO dress presentably. Clean it up. No Hawaiian shirts. And go easy on the hair product.

-- DO know how to talk to a woman. Bad line: "If your name weren't Ronni, what name would you want?" Good line: "You're a widow but out dating again? That's good for us men."

-- DON'T leave a woman sitting alone because you're too shy to come over during the break for buffet. For God's sake, it's speed dating. What did you sign up for?

-- DON'T talk about marriage on a five-minute speed date.

-- DO come up with a reason for why you're in your 50s (or 60s) and have never met the right woman. It can be finessed.

-- DON'T accidentally take your date's drink to the next table (and next date) with you. Pay attention to what you're doing.

-- DO know your selling points. If it's not your career -- and it can't always be -- come up with something you're good at.

-- DO act interested in what she's saying. Unless you just don't care.

But I am not giving up. I've told friends to keep on the lookout for suitable partners for me. I also have a couple of first dates next week with men I've met online. And yes -- expect me to get there first.

Have you re-entered the dating pool in middle age? What are some of the unique challenges you've faced? Share your experiences in the comments section below.